This invention relates to 5-deoxy, 5-C-alkyl, 5-C-alkenyl and 5-C-alkylidene-5-deoxy-3-O-arylmethyl and substituted arylmethyl-1,2,-O-ethylene-alpha-D-xylofuranose derivatives and to the application of such compounds as herbicides and plant growth regulators. The invention also relates to the preparation of such compounds.
The laboratory preparation of 3-O-benzyl-5-deoxy-1,2-O-isopropylidene-alpha-D-xylofuranose for the purpose of conducting academic sugar studies is referenced in Tetrahedron Letters No. 26, pp. 2447-2448 (1979). The preparation of 3-O-benzyl-5-deoxy-1,2-O-isopropylidene-5-C-propyl-alpha-D-xylofuranose as an intermediate in the multistep synthesis of the antibiotic (-)-Canadensolide is described in Tetrahedron Letters No. 35, pp. 3233-3236 (1978) and J. Chem. Soc. Jap., Chem. Ind. Chem. 1981(5), 769-775. The laboratory preparation of 3-O-benzyl-5-deoxy-5-C-methylene-1,2-O-isopropylidene-alpha-D-xylofuranose relative to certain academic studies is described in numerous publications, including Synthesis 636 (1980); Tetrahedron Letters 4841 (1979); Carbohydrate Research 48, 143 (1976) Tetrahedron Letters 2623 (1975); Helv. Chim Acta 1303 (1973); J. Chem. Soc. Perkin Trans I. 38 (1973); Carbohyd. Research 26, 230 (1973); Carbohyd. Research 22, 227 (1972); Carbohyd. Research, 215 (1970); J. Amer. Chem. Soc. 78, 2846 (1956); Carbohyd. Res. 7, 161 (1968), Methods in Carbohyd. Chem. Vol. VI 297 (1972).
The laboratory preparation of 3-O-benzyl-5-deoxy-5-C-propylidene-1,2-O-isopropylidene-alpha-D-xylofurano se is described in Tetrahedron Letters 3233 (1978) and the laboratory preparation of 3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-5-C-methylene-alpha-D-xylo-hex ofuranose is described in Helvetica Chimica Acta 58, 1501 (1975).
The laboratory preparation of 3-O-benzyl-6,7-dideoxy-1,2-O-isopropylidene-alpha-D-xylo-heptofuranos-5-ul ose and/or 3-O-benzyl-6-deoxy-1,2-O-isopropylidenealpha-D-xylo-hexofuranos-5-ulose for academic studies is described in Carbohydrate Research 31 (1973), pages 387-396; Carbohydrate Research 29 (1973), pages 11-323; Bulletin of the Chemical Society of Japan, 51 (12) (1978), pages 3595-3598; Journal of Organic Chemistry 44 (1979), pages 4294-4299; Journal of Organic Chemistry 46, (1981), pages 1296-1309; Helv. Chim. Acta 56, 1802 (1973); Carbohydrate Research 26, 441 (1973); Chem. Ber. 102, 820 (1969) and J. Org. Chem. 27, 2107 (1962).
U.S. Pat. Nos. 4,116,669, 4,146,384 and 4,330,320 and German Patent DS 2,860,975 disclose a broad range of tetrahydrofuran derivatives and attribute herbicidal activity to these derivatives. U.S. Pat. Nos. 3,919,252, 4,004,911 and 4,207,088 disclose dioxalane derivatives and dioxane derivatives and attribute grass herbicidal activity to these derivatives. The sodium salt of 2,3:4,6-bis-O-(1-methylethylidene)-O-(L-xylo-2-hexulofuranosonic acid) is sold as a pinching agent for azaleas and ornamentals and a growth retardant for shrubs, hedges and ground covers and is disclosed in U.S. Pat. No. 4,007,206.
The application of 5-C-alkyl-3-O-benzyl-1,2-O-isopropylidene alpha-D-xylo-pentodialdofuranose as herbicides and plant growth regulators is described by B. McCaskey in commonly assigned copending application Ser. No. 387,590 filed June 11, 1982.
In my copending applications Ser. No. 409,236, filed Aug. 18, 1982, now U.S. Pat. No. 4,429,119, and Ser. No. 559,126, filed Dec. 7, 1983, I disclosed certain optionally substituted 5-deoxy-3-O-arylmethyl-1,2-O-alkylidene-alpha-D-xylofuranose derivatives which are useful as herbicides and plant growth regulators.